Organic metal complex, and organic light emitting device and display apparatus using the same

ABSTRACT

and a partial structure ML′n represents a structure including a monovalent bidentate ligand.

TECHNICAL FIELD

The present invention relates to an organic metal complex, and anorganic light emitting device and a display apparatus using the organicmetal complex.

BACKGROUND ART

An organic light emitting device is a device in which a thin filmincluding a fluorescent organic compound is sandwiched between an anodeand a cathode. Further, electrons and holes are injected from therespective electrodes to generate exciton of the fluorescent compound,whereby the organic light emitting device emits light when the excitonreturns to a ground state.

Recent progress of an organic light emitting device is remarkable, andthe characteristics of the device enable a light emitting device with ahigh luminance at a low applied voltage, a variety of emissionwavelengths, high-speed responsiveness, thin and light weight. From thisfact, it is suggested that the organic light emitting device havepotential to find use in a wide variety of applications.

However, the present situation calls for optical output with even higherluminance or higher conversion efficiency. In addition, many problemsstill remain to be solved regarding durability against the change overtime due to long-term use, deterioration caused by atmospheric gascontaining oxygen, moisture, or the like.

Further, when considering application to a full color display or thelike, the present art is still insufficient against problems relating tothe needs for light emission of a red color with high color purity andhigh efficiency. On the other hand, an organic light emitting devicehaving, in particular, high color purity, high light emittingefficiency, and high durability, and a material realizing the organiclight emitting device have been demanded.

By the way, as a light emitting material which can utilize lightemission from a triplet excitation state, an iridium (Ir) complex hasbeen proposed. Examples of the Ir complex to be used as the lightemitting material herein include the Ir complexes disclosed in Macromol.Symp. 125, 1-48 (1997), “Improved energy transfer inelectrophosphorescent device”, D. F. O'Brien, et al., Applied PhysicsLetters, Vol. 74, No. 3, p. 422 (1999), “Very high-efficiency greenorganic light-emitting devices based on electrophosphorescence”, M. A.Baldo, et al., Applied Physics Letters, Vol. 75, No. 1, p. 4 (1999),Japanese Patent Application Laid-Open No. 2001-247859, and JapanesePatent Application Laid-Open No. 2005-344124.

DISCLOSURE OF THE INVENTION

The present invention is accomplished to solve the above-mentionedproblems of the conventional art. That is, an object of the presentinvention is to provide a novel Ir complex. Further, another object ofthe present invention is to provide an organic light emitting devicehaving light emission with high efficiency and high luminance, andhaving durability.

An organic metal complex of the present invention has a structurerepresented by the following general formula (1):

ML_(m)L′_(n)  (1)

where: M represents a metal atom selected from Ir, Pt, Rh, Os, and Zn; Land L′, which are different from each other, each represent a bidentateligand; m represents an integer of 1 to 3 and n represents an integer of0 to 2, provided that m+n is 3; a partial structure ML_(m) represents astructure represented by the following general formula (2):

where: A represents a structure represented by any one of the followinggeneral formulae (3) to (7), which has, as a basic skeleton, one ofbenzo[f]quinoline, benzo[h]quinoline, benzo[f]isoquinoline, andbenzo[h]isoquinoline:

where R₁ to R₄₀, which may be identical to or different from each other,each represent a hydrogen atom, a halogen atom, a substituted orunsubstituted alkyl group, an alkoxy group, an aralkyl group, asubstituted amino group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group, and adjacentsubstituents among R₁ to R₄₀ may be bonded to form a ring; and

B represents a benzene ring which may have a substituent, a fused ringwhich may have a substituent, a vinyl group which may have asubstituent, or a heterocycle which may have a substituent; and

a partial structure ML′_(n) represents a structure including amonovalent bidentate ligand.

According to the present invention, there can be provided the novel Ircomplex and the organic light emitting device having light emission withhigh efficiency and high luminance, and having durability.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a diagram illustrating schematically a configuration exampleof a display apparatus including an organic light emitting device of thepresent invention and a driving unit, which is an embodiment of adisplay apparatus.

FIG. 2 is a circuit diagram illustrating a circuit which constitutes oneof the pixels arranged on the display apparatus shown in FIG. 1.

FIG. 3 is a schematic diagram illustrating an example of across-sectional structure of a TFT substrate which is used in thedisplay apparatus shown in FIG. 1.

FIG. 4 is a diagram illustrating a PL spectrum of Exemplified CompoundB-20 in 1×10⁻⁵ mol/l toluene solution.

FIG. 5 is a diagram illustrating a PL spectrum of Exemplified CompoundB-1 in 1×10⁻⁵ mol/l toluene solution.

FIG. 6 is a diagram illustrating a PL spectrum of Exemplified CompoundA-30 in 1×10⁻⁵ mol/l toluene solution.

FIG. 7 is a diagram illustrating a PL spectrum of Exemplified CompoundA-1 in 1×10⁻⁵ mol/l toluene solution.

BEST MODE FOR CARRYING OUT THE INVENTION

An organic metal complex of the present invention is an organic metalcomplex having a structure represented by the following general formula(1):

ML_(m)L′_(n)  (1)

where: M represents a metal atom selected from Ir, Pt, Rh, Os, and Zn;

L_(m) and L′_(n), which are different from each other, each represent abidentate ligand, and specific structures of L and L′ are describedbelow; and

m represents an integer of 1 to 3 and n represents an integer of 0 to 2,provided that m+n is 3.

Hereinafter, the specific structure of L is described. A partialstructure ML_(m) of the complex containing L is represented by thefollowing general formula (2):

where A represents a structure represented by any one of the followinggeneral formulae (3) to (7), which has, as a basic skeleton, one ofbenzo[f]quinoline, benzo[h]quinoline, benzo[f]isoquinoline, andbenzo[h]isoquinoline:

where R₁ to R₄₀ each represent a hydrogen atom, a halogen atom, asubstituted or unsubstituted alkyl group, an alkoxy group, an aryloxygroup, an aralkyl group, a substituted amino group, a substituted orunsubstituted aryl group, or a substituted or unsubstituted heterocyclicgroup.

Examples of the halogen atom represented by R₁ to R₄₀ include fluorine,chlorine, bromine, and iodine.

Examples of the alkyl group represented by R₁ to R₄₀ include, but ofcourse are not limited to, a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a t-butyl group, asec-butyl group, an octyl group, a 1-adamantyl group, and a 2-adamantylgroup.

Examples of the alkoxy group represented by R₁ to R₄₀ include, but ofcourse are not limited to, a methoxy group, an ethoxy group, a propoxygroup, a 2-ethyl-octyloxy group, and a benzyloxy group.

Examples of the aryloxy group represented by R₁ to R₄₀ include, but ofcourse are not limited to, a phenoxy group, a 4-tert-butyl phenoxygroup, and a thienyloxy group.

Examples of the aralkyl group represented by R₁ to R₄₀ include, but ofcourse are not limited to, a benzyl group.

Examples of the substituted amino group represented by R₁ to R₄₀include, but of course are not limited to, an N-methylamino group, anN-ethylamino group, an N,N-dimethylamino group, an N,N-diethylaminogroup, an N-methyl-N-ethylamino group, an N-benzylamino group, anN-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilinogroup, an N,N-diphenylamino group, an N,N-dinaphthylamino group, anN,N-difluorenylamino group, an N-phenyl-N-tolylamino group, anN,N-ditolylamino group, an N-methyl-N-phenylamino group, anN,N-dianisolylamino group, an N-mesityl-N-phenylamino group, anN,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group,and an N-phenyl-N-(4-trifluoromethylphenyl)amino group.

Examples of the aryl group represented by R₁ to R₄₀ include, but ofcourse are not limited to, a phenyl group, a naphthyl group, an indenylgroup, a pyrenyl group, an indacenyl group, an acenaphthenyl group, aphenanthryl group, a fluoranthenyl group, a triphenylenyl group, achrysenyl group, a naphthacenyl group, a perylenyl group, a biphenylgroup, a terphenyl group, and a fluorenyl group.

Examples of the heterocyclic group represented by R₁ to R₄₀ include, butof course are not limited to, a pyridyl group, an oxazolyl group, anoxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolylgroup, an acridinyl group, and a phenanthrolyl group.

Examples of the substituent that the alkyl group, the aryl group, andthe heterocyclic group each may further have include, but of course arenot limited to: alkyl groups such as a methyl group, an ethyl group, anda propyl group; aralkyl groups such as a benzyl group; aryl groups suchas a phenyl group, a biphenyl group, a tetrakis(9,9-dimethylfluorenyl)group; heterocyclic groups such as a pyridyl group and a pyrrolyl group;amino groups such as a dimethylamino group, a diethylamino group, adibenzylamino group, a diphenylamino group, and a ditolylamino group;alkoxyl groups such as a methoxyl group, an ethoxyl group, and apropoxyl group; aryloxyl groups such as a phenoxyl group; and halogenatoms such as fluorine, chlorine, bromine, and iodine; and a cyanogroup.

The substituents represented by R₁ to R₈, R₉ to R₁₆, R₁₇ to R₂₄, R₂₅ toR₃₂, or R₃₃ to R₄₀ may each be identical to or different from oneanother.

In addition, of those substituents represented by R₁ to R₈, R₉ to R₁₆,R₁₇ to R₂₄, R₂₅ to R₃₂, or R₃₃ to R₄₀, adjacent substituents may bebonded to form a ring such as a benzene ring, an indene ring, anaphthalene ring, a pyridine ring, a pyrrole ring, or a cyclohexyl ring.

In the formula (2), B represents a benzene ring which may have asubstituent, a fused ring which may have a substituent, a vinyl groupwhich may have a substituent, or a heterocycle which may have asubstituent.

Examples of the substituent that the benzene ring, fused ring, vinylgroup, and heterocycle each may further have include halogen atoms,substituted or unsubstituted alkyl groups, alkoxy groups, aryloxygroups, aralkyl groups, substituted amino groups, substituted orunsubstituted aryl groups, and substituted or unsubstituted heterocyclicgroups.

Examples of the halogen atom include fluorine, chlorine, bromine, andiodine.

Examples of the alkyl groups include, but of course are not limited to,a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, a tert-butyl group, a sec-butyl group, an octyl group,a 1-adamantyl group, and a 2-adamantyl group.

Examples of the alkoxy group include, but of course are not limited to,a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxygroup, and a benzyloxy group.

Examples of the aryloxy group include, but of course are not limited to,a phenoxy group, a 4-tert-butyl phenoxy group, and a thienyloxy group.

Examples of the aralkyl group include, but of course are not limited to,a benzyl group.

Examples of the substituted amino group include, but of course are notlimited to, an N-methylamino group, an N-ethylamino group, anN,N-dimethylamino group, an N,N-diethylamino group, anN-methyl-N-ethylamino group, an N-benzylamino group, anN-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilinogroup, an N,N-diphenylamino group, an N,N-dinaphthylamino group, anN,N-difluorenylamino group, an N-phenyl-N-tolylamino group, anN,N-ditolylamino group, an N-methyl-N-phenylamino group, anN,N-dianisolylamino group, an N-mesityl-N-phenylamino group, anN,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group,and an N-phenyl-N-(4-trifluoromethylphenyl)amino group.

Examples of the aryl group include a phenyl group, a naphthyl group, anindenyl group, a pyrenyl group, an indacenyl group, an acenaphthenylgroup, a phenanthryl group, a fluoranthenyl group, a triphenylenylgroup, a chrysenyl group, a naphthacenyl group, a perylenyl group, abiphenyl group, a terphenyl group, and a fluorenyl group.

Examples of the heterocyclic group include, but of course are notlimited to, a pyridyl group, an oxazolyl group, an oxadiazolyl group, athiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinylgroup, and a phenanthrolyl group.

Examples of the substituent that the alkyl group, the aryl group, andthe heterocyclic group each may further have include: alkyl groups suchas a methyl group, an ethyl group, and a propyl group; aralkyl groupssuch as a benzyl group; aryl groups such as a phenyl group, a biphenylgroup, and a tetrakis(9,9-dimethylfluorenyl) group; heterocyclic groupssuch as a pyridyl group and a pyrrolyl group; amino groups such as adimethylamino group, a diethylamino group, a dibenzylamino group, adiphenylamino group, and a ditolylamino group; alkoxyl groups such as amethoxyl group, an ethoxyl group, and a propoxyl group; aryloxyl groupssuch as a phenoxyl group; and halogen atoms such as fluorine, chlorine,bromine, and iodine; and a cyano group.

Hereinafter, the specific structure of L′ in the formula (1) isdescribed. A partial structure ML′_(n) of the complex containing L′ is astructure containing monovalent bidendate ligand (L′).

Here, specific examples of the monovalent bidentate ligand are notparticularly limited, but include ligands each having, as a basicskeleton, acetylacetone, phenylpyridine, picolinic acid, oxalate, orsalene.

The organic metal complex of the present invention is preferably theorganic metal complex represented by the formula (1) where M representsIr, the partial structure ML_(m) represents a structure represented bythe following general formula (8) or (9), and the partial structureML′_(n) represents a structure represented by any one of the followinggeneral formulae (10) to (12).

First, the partial structure ML_(m) is described. Note that m has thesame meaning as m in the formula (1).

In the formulae (8) and (9), R₄₁ to R₆₄ each represent a hydrogen atom,a halogen atom, a substituted or unsubstituted alkyl group, an alkoxygroup, an aralkyl group, an amino group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heterocyclic group.

Examples of the halogen atom represented by R₄₁ to R₆₄ include fluorine,chlorine, bromine, and iodine.

Examples of the alkyl group represented by R₄₁ to R₆₄ include, but ofcourse are not limited to, a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a tert-butyl group, asec-butyl group, an octyl group, a 1-adamantyl group, and a 2-adamantylgroup.

Examples of the alkoxy group represented by R₄₁ to R₆₄ include, but ofcourse are not limited to, a methoxy group, an ethoxy group, a propoxygroup, a 2-ethyl-octyloxy group, and a benzyloxy group.

Examples of the aryloxy group represented by R₄₁ to R₆₄ include, but ofcourse are not limited to, a phenoxy group, a 4-tert-butyl phenoxygroup, and a thienyloxy group.

Examples of the aralkyl group represented by R₄₁ to R₆₄ include, but ofcourse are not limited to, a benzyl group.

Examples of the substituted amino group represented by R₄₁ to R₆₄include, but of course are not limited to, an N-methylamino group, anN-ethylamino group, an N,N-dimethylamino group, an N,N-diethylaminogroup, an N-methyl-N-ethylamino group, an N-benzylamino group, anN-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilinogroup, an N,N-diphenylamino group, an N,N-dinaphthylamino group, anN,N-difluorenylamino group, an N-phenyl-N-tolylamino group, anN,N-ditolylamino group, an N-methyl-N-phenylamino group, anN,N-dianisolylamino group, an N-mesityl-N-phenylamino group, anN,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group,and an N-phenyl-N-(4-trifluoromethylphenyl)amino group.

Examples of the aryl group represented by R₄₁ to R₆₄ include a phenylgroup, a naphthyl group, an indenyl group, a pyrenyl group, an indacenylgroup, an acenaphthenyl group, a phenanthryl group, a fluoranthenylgroup, a triphenylenyl group, a chrysenyl group, a naphthacenyl group, aperylenyl group, a biphenyl group, a terphenyl group, and a fluorenylgroup.

Examples of the heterocyclic group represented by R₄₁ to R₆₄ include,but of course are not limited to, a pyridyl group, an oxazolyl group, anoxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolylgroup, an acridinyl group, and a phenanthrolyl group.

Examples of the substituent that the alkyl group, the aryl group, andthe heterocyclic group each may further have include: alkyl groups suchas a methyl group, an ethyl group, and a propyl group; aralkyl groupssuch as a benzyl group; aryl groups such as a phenyl group, a biphenylgroup, and a tetrakis(9,9-dimethylfluorenyl) group; heterocyclic groupssuch as a pyridyl group and a pyrrolyl group; amino groups such as adimethylamino group, a diethylamino group, dibenzylamino group, adiphenylamino group, and a ditolylamino group; alkoxyl groups such as amethoxyl group, an ethoxyl group, and a propoxyl group; aryloxyl groupssuch as a phenoxyl group; and halogen atoms such as fluorine, chlorine,bromine, and iodine; and a cyano group.

The substituents represented by R₄₁ to R₅₂ or R₅₃ to R₆₄ may each beidentical to or different from one another.

In addition, of those substituents represented by R₄₁ to R₅₂ or R₅₃ toR₆₄, adjacent substituents may be bonded to form a ring such as abenzene ring, an indene ring, a naphthalene ring, a pyridine ring, apyrrole ring, or a cyclohexyl ring.

Next, the partial structure ML′_(n) is described. Note that n has thesame meaning as n in the formula (1).

In the formulae (10) to (12), R₆₅ to R₇₉ each represent a hydrogen atom,a halogen atom, a substituted or unsubstituted alkyl group, an alkoxygroup, an aralkyl group, a substituted amino group, a substituted orunsubstituted aryl group, or a substituted or unsubstituted heterocyclicgroup.

Examples of the halogen atom represented by R₆₅ to R₇₉ include fluorine,chlorine, bromine, and iodine.

Examples of the alkyl group represented by R₆₅ to R₇₉ include, but ofcourse are not limited to, a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a tert-butyl group, asec-butyl group, an octyl group, a 1-adamantyl group, and a 2-adamantylgroup.

Examples of the alkoxy group represented by R₆₅ to R₇₉ include, but ofcourse are not limited to, a methoxy group, an ethoxy group, a propoxygroup, a 2-ethyl-octyloxy group, and a benzyloxy group.

Examples of the aryloxy group represented by R₆₅ to R₇₉ include, but ofcourse are not limited to, a phenoxy group, a 4-tert-butyl phenoxygroup, and a thienyloxy group.

Examples of the aralkyl group represented by R₆₅ to R₇₉ include, but ofcourse are not limited to, a benzyl group.

Examples of the substituted amino group represented by R₆₅ to R₇₉include, but of course are not limited to, an N-methylamino group, anN-ethylamino group, an N,N-dimethylamino group, an N,N-diethylaminogroup, an N-methyl-N-ethylamino group, an N-benzylamino group, anN-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilinogroup, an N,N-diphenylamino group, an N,N-dinaphthylamino group, anN,N-difluorenylamino group, an N-phenyl-N-tolylamino group, anN,N-ditolylamino group, an N-methyl-N-phenylamino group, anN,N-dianisolylamino group, an N-mesityl-N-phenylamino group, anN,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group,and an N-phenyl-N-(4-trifluoromethylphenyl)amino group.

Examples of the aryl group represented by R₆₅ to R₇₉ include a phenylgroup, a naphthyl group, an indenyl group, a pyrenyl group, an indacenylgroup, an acenaphthenyl group, a phenanthryl group, a fluoranthenylgroup, a triphenylenyl group, a chrysenyl group, a naphthacenyl group, aperylenyl group, a biphenyl group, a terphenyl group, and a fluorenylgroup.

Examples of the heterocyclic group represented by R₆₅ to R₇₉ include,but of course are not limited to, a pyridyl group, an oxazolyl group, anoxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolylgroup, an acridinyl group, and a phenanthrolyl group.

Examples of the substituent that the alkyl group, the aryl group, andthe heterocyclic group each may further have include: alkyl groups suchas a methyl group, an ethyl group, and a propyl group; an aralkyl groupsuch as a benzyl group; aryl groups such as a phenyl group, a biphenylgroup, and a tetrakis(9,9-dimethylfluorenyl) group; heterocyclic groupssuch as a pyridyl group and a pyrrolyl group; amino groups such as adimethylamino group, a diethylamino group, a dibenzylamino group, adiphenylamino group, and a ditolylamino group; alkoxyl groups such as amethoxyl group, an ethoxyl group, and a propoxyl group; aryloxyl groupssuch as a phenoxyl group; halogen atoms such as fluorine, chlorine,bromine, and iodine; and a cyano group.

The substituents represented by R₆₅ to R₇₂, R₇₃ to R₇₆, or R₇₇ to R₇₉may each be identical to or different from one another.

In addition, of those substituents represented by R₆₅ to R₇₂, R₇₅ toR₇₆, or R₇₇ to R₇₉, adjacent substituents may be bonded to form a ringsuch as a benzene ring, an indene ring, a naphthalene ring, a pyridinering, a pyrrole ring, or a cyclohexyl ring.

Next, the synthesis method for an organic metal complex of the presentinvention is described. The organic metal complexes represented by thegeneral formulae (1) and (6) to (9) can be synthesized with reference toJ. Org. Chem. (2001), Vol. 66, 8042-8051, Org. Lett., Vol. 7, No. 18,2005, Org. Lett., Vol. 7, No. 23, 2005, Chimica Therapeutica (1971),Vol. 6(1), 48-9, and J. Org. Chem. (1958), Vol. 23268-71.

Specifically, the organic metal complex can be synthesized through thefollowing steps.

(i) synthesis of an organic compound serving as a ligand(ii) Synthesis of an organic metal complex

Here, the organic compound serving as a ligand can be synthesized by anyone of Synthetic Routs 1 to 3, for example.

Synthetic Rout 1

Synthetic Route 2

Synthetic Route 3

Note that, whichever of Synthetic Routes 1 to 3 is employed, an organiccompound as a starting substance is not limited to one of Compounds G1to G6 represented in Synthetic Routes 1 to 3.

Here, in the case of employing Synthetic Route 1, combinations of abromo body as a starting substance, an arylacetylene as a startingsubstance, and a ligand to be synthesized are given in Table 1 below,for example, but the present invention is not limited thereto.

TABLE 1 Bromo body Arylacetylene Ligand to be synthesized 1

2

3

4

5

6

7

8

On the other hand, in the case of employing Synthetic Route 2,combinations of a chloro body as a starting substance, a boronic acid oran organic metal compound as a starting substance, and a ligand to besynthesized are given in Table 2 below, for example, but the presentinvention is not limited thereto.

TABLE 2 Boronic acid or organic Chloro body metal compound Ligand to besynthsized  9

10

11

12

13

14

15

16

17

18

19

20

On the other hand, in the case of employing Synthetic Route 3,combinations of a benzoquinoline derivative as a starting substance, alithium compound as a starting substance, and a ligand to be synthesizedare given in Table 3 below, for example, but the present invention isnot limited thereto.

TABLE 3 Benzoquinoline derivative Lithium compound Ligand tobesynthesized 21

22

23

24

25

26

27

28

29

30

The various ligands synthesized by Synthetic Routes 1 to 3 are used,whereby the organic metal complex of the present invention can besynthesized by any one of Synthetic Routes 4 to 6.

Synthetic Route 4

Synthetic Route 5

Synthetic Route 6

Here, in the case of employing Synthetic Route 4, an organic metalcomplex formed of two or more kinds of ligands can be synthesized. WhenSynthetic Route 4 is employed, in a second step reaction, picolinic acidor tert-butyl acetylacetone may be used instead of acetylacetone. Inaddition, in a third step reaction, a ligand such as phenyl pyridine maybe used instead of a ligand synthesized by any one of Synthetic Routes 1to 3 (phenyl benzoquinoline, phenyl benzoisoquinoline).

As described above, the organic metal complex of the present inventionincludes one kind or two kinds of bidentate ligands and a metal atomsuch as Ir. In addition, the bidentate ligand has, as a basic skeleton,a heterocyclic skeleton containing a nitrogen atom which forms acoordinate bond with the metal atom. Specifically, as a basic skeleton,the bidentate ligand has, as a basic skeleton, one of benzo[f]quinoline,benzo[h]quinoline, benzo[f]isoquinoline, and benzo[h]isoquinoline, whichare shown below.

The above-mentioned heterocycle is incorporated as a basic skeleton ofthe bidentate ligand, whereby a light emitting material having highefficiency can be obtained without an emission wavelength beinglengthened when a quinoline or an isoquinoline skeleton is used.

As a measure for improving light emitting efficiency of the lightemitting material, there are given a measure for suppressingdeactivation due to a nonradiative process (hereinafter, referred to asfirst measure) and a measure for increasing oscillator strength of thematerial itself (hereinafter, referred to as second measure).

As the first measure, decreasing the number of freely-rotating sites inmolecules and the like have been generally known. On the other hand, thesecond measure largely depends on a structure of the complex or a basicstructure of the ligand, whereby it is difficult to control theoscillator strength actively. In particular, increasing the oscillatorstrength while the emission wavelength is controlled is an importantfactor in the organic light emitting device, but difficult in practice.

Here, in the organic metal complex of the present invention, a conjugateplane at a pyridine side of the ligand is extended away from the metalatom, and hence a quantum efficiency of the complex itself can beincreased.

On the other hand, in the case where electron transition of the excitonwhich is generated by allowing the light emitting material such as anorganic metal complex to excite has a metal to ligand charge transfer(MLCT) property, an electron is transferred from the metal atom side toa bidentate ligand side. When Ir(piq)₃ and Compound A1 are taken forexample, a conjugate plane that a molecular structure present at anitrogen-metal coordination side of the bidentate ligand has isextended, and a center of gravity of the conjugate plane is moved to adirection away from the metal atom. From the foregoing, it was foundthat lengthening a migration length of the electron which transfers fromthe metal atom to the ligand upon the excitation of the complex waseffective for improving the light emitting efficiency. This may bebecause, owing to the electron transfer from the metal to the ligand andfurther away therefrom, a dipolar moment of the complex upon theexcitation is increased and hence the oscillator strength is improved.

In order to examine the fact, a molecular orbital for a relationship ofa distance between the conjugate plane that the metal atom and theligand in the organic metal complex have and the oscillator strength wascalculated. For example, a molecular orbital (nonempirical molecularorbital calculation program: Gaussian, basis function: B3PW91/LANL2DZ)for each organic metal complex represented by one of the followingformula was calculated.

As a result, the calculational oscillator strength of Compound A1 wasfound to be 1.5 times to twice larger than that of Ir(piq)₃. Similarly,it was found that each calculational oscillator strength of Compound B1and C1 was 1.5 times to twice larger than that of Ir(p-3iq)₃ and eachcalculational oscillator strength of Compound D1 and E1 was 1.5 times totwice larger than that of Ir(pq)₃. However, those results were theresults obtained from calculation, and actual quantum efficiency of thecompound may not be reflected to the calculation results. However, theresult can be an evidence to support that light emitting characteristicstend to improve due to the structure.

However, when ring structures such as a benzene ring are fused simply, aconjugate length is lengthened for fused components, and therefore,there is the case where the emission wavelength of the compound itselfis lengthened. For example, Ir(p-bgiq)₃ represented below lengthen thewavelength by 100 nm or more with respect to Ir(p-3iq)₃ and the emissionwavelength of the compound itself becomes 650 nm or more.

Therefore, luminescent color becomes dark red and the emissionwavelength is lengthened too much, so the compound is not a suitablelight emitting material for an organic EL display.

Then, when the ring structures such as a benzene ring are fused, asshown in the above-mentioned Compounds A1, B1, C1, D1, and E1,heterocyclic skeletons each having a nitrogen atom which forms acoordinate bond with a metal atom are fused in a non-linear form. Withthe non-linear form, it was found that the oscillator strength could beincreased without the emission wavelength being lengthened.

In this point, when the number of the benzene ring present at thenitrogen-metal coordination side of the bidentate ligand is increased,the number of the benzene ring is increased preferably at a positionwhere the benzene ring is not linear with respect to quinoline rings orisoquinoline rings as shown in A1, B1, C1, D1, and E1. Further, forincreasing the oscillator strength, the benzene ring is fused to form aring preferably at as far away as possible from the metal. From theforegoing, the benzene ring is fused to form a ring preferably atf-position or h-position of the quinoline ring or the isoquinoline ring.In particular, each structure of Compounds A1 and B1 can additionallyincrease the oscillator strength by such points that a center of theconjugate plane at the pyridine side is as far away as possible from themetal atom and a moment of the metal and pyridine and a moment of themetal and the gravity center of conjugate are superposed.

On the other hand, the reason why the wavelength is not lengthened,compared to the case of the quinoline ring or the isoquinoline ring,when a structure at the nitrogen-metal side of the ligand has thestructure like Compounds A1, B1, C1, D1, and E1 lies in theabove-mentioned fact.

In the organic metal complex of the present invention, an unsharedelectron pair that the nitrogen atom present in the quinoline skeletonor the isoquinoline skeleton has is used in forming a coordinate bondwith the metal atom. Therefore, the nitrogen atom may behave similarlyas the carbon atom. In the foregoing, a relationship among threeskeletons, i.e., the quinoline skeleton, the isoquinoline skeleton, andthe skeleton in which a ring structure is fused to those skeletons, issimilar to a relationship among three skeletons, i.e., naphthalene,anthracene, and phenanthrene.

Here, the following description is written in “Handbook ofphotochemistry” published by Dekker: a triplet excitation energy (T₁) ofanthracene in which a benzene ring is fused linearly to naphthalene is672 nm and the wavelength thereof is indicated to be largely lengthenedwhile T₁ of naphthalene is 469 nm; on the other hand, T₁ of phenanthrenein which a benzene ring is fused non-linearly to naphthalene is 460 nm,and is indicated to be higher than that of naphthalene.

Taking the above-mentioned fact into consideration, emission wavelengthsof benzo[f]quinoline, benzo[h]quinoline, benzo[f]isoquinoline, andbenzo[h]isoquinoline corresponding to phenanthrene may not be lengthenedcompared to quinoline and isoquinoline corresponding to naphthalene.Accordingly, a complex containing, as a ligand, benzo[f]quinoline,benzo[h]quinoline, benzo[f]isoquinoline, or benzo[h]isoquinoline isfound to have the following characteristics: while a wavelength of thecomplex is not lengthened with respect to a complex containing aisoquinoline skeleton or a quinoline skeleton, an oscillator strength ofthe complex itself can be increased and an emission quantum efficiencyis improved. Therefore, the complex containing, as a basic skeleton,benzo[f]quinoline, benzo[h]quinoline, benzo[f]isoquinoline, orbenzo[h]isoquinoline is excellent as a light emitting material of aphosphorous light emitting material or the like such as an Ir complex.

In addition, Compounds A1, B1, C1, D1, and E1 each have the followingproperties.

Compound A1 without introducing a substituent can emit a red light,which has a slightly shorter wavelength than that of Ir(piq)₃, and thequantum efficiency is also high. Accordingly, when Compound A1 is usedas a constituent material of the organic light emitting device, ahigh-performance device can be provided. In addition, by introducing asubstituent, the emission wavelength can be controlled.

Compounds B1 and C1 without introducing a substituent can emit a greenlight which has a slightly shorter wavelength than that of Ir(p-3iq)₃and the quantum efficiency is high. In addition, by introducing asubstituent, the emission wavelength can be controlled.

Compounds D1 and E1 without introducing a substituent can emit an orangelight which has a slightly shorter wavelength than that of Ir(pq)₃ andthe quantum efficiency is high. In addition, by introducing asubstituent, the emission wavelength can be controlled.

Thus, a light having a wavelength of green to red, which is important inthe organic light emitting device, can be efficiently extracted byselecting a compound appropriately from Compounds A1, B1, C1, D1, andE1.

In addition, it is possible to introduce a substituent into a ligandforming the organic metal complex of the present invention in order toimpart steric hindrance to the complex. Thus, a solubility of the ligandupon synthesis of the complex is improved. In addition, from theforegoing, concentration quenching is suppressed, so doping at highconcentration is enabled and the light emitting efficiency is expectedto be improved when the organic metal complex is used as a constituentmaterial of the device. Here, examples of the substituent for impartingthe steric hindrance to the complex include substituents which avoidapproaching of luminous ligands to each other, such as a methyl group, atert-butyl group, and a phenyl group, and substituents which inducerepulsion of molecules to each other, such as halogen atoms. Byintroducing those substituents, even when doping of concentration ashigh as 5 wt % or more with respect to matrix is occurred, a light canbe emitted without reducing a light emitting efficiency.

On the other hand, when the ring structure such as a benzene ring isfused linearly as the above-mentioned Ir(p-bgiq)₃, a part which is weakto oxidation and is highly reactive such as 9-position or 10-position inan anthracene skeleton, for example, is generated. Therefore, asIr(p-bgiq)₃, a compound having a skeleton in which ring structures suchas a benzene ring are linearly fused may not be preferred as aconstituent material for an organic light emitting device.

By the way, in the ligand forming the organic metal complex of thepresent invention, as a basic skeleton containing a carbon atom whichforms a coordinate bond with a metal atom, a benzene ring is mainlyexemplified, but a skeleton other than a benzene ring may also be usedas long as the skeleton has the structure containing a carbon atom whichforms a coordinate bond with a metal atom. By appropriately controllingthe basic skeleton containing a carbon atom which forms a coordinatebond with a metal atom, an emission wavelength of the organic metalcomplex itself can be controlled. Examples of the basic skeleton includea naphthalene ring, a fluorene ring, a carbazole ring, a vinyl skeleton,and a pyridine ring, in addition to the benzene ring.

In addition, the organic metal complex of the present invention may havea molecular structure in which ligands of the same kind are coordinatedto the metal atom or may have a molecular structure in which two kindsof ligands having different structures are coordinated from a viewpointof controlling a molecular weight and a wavelength.

Here, in the case where the complex has the structure in which ligandsof the same kind are coordinated to the metal atom, the complex has highsymmetric property to the metal atom, and hence has such high heatstability and high electrical stability that the metal complex is noteasily decomposed upon deposition. In addition, introduction of asubstituent enables lengthening a distance from another light emittingmolecules. Therefore, even with doping of as high concentration as 10%or higher to 100%, a light can be emitted while reduction of the lightemitting efficiency is suppressed. On the other hand, in the case wherethe complex has the structure in which two kinds of ligands havingdifferent structures are coordinated to the metal atom, the complex hassuch properties that a deposition temperature can be adjusted byadjustment of the molecular weight and the emission wavelength can becontrolled by using an electronic effect of a ligand which does not emita light. In addition, the number of ligands relating to light emittingcan be reduced from 3 ligands to 2 ligands or 1 ligand. Therefore, aconcentration quenching can be expected to be suppressed and even withdoping of as high concentration as 10% or higher to 100%, a light can beemitted while reduction of the light emitting efficiency is suppressed.

In addition, the organic metal complex of the present invention hassteric constitutional isomers, i.e., a fac body and a mer body. Theorganic metal complex of the present invention may have one of thestructures but preferably the fac body which may generally have highquantum efficiency. However, in the case where the complex has thestructure in which two kinds of ligands having different structures arecoordinated to the metal atom, even the mer body such as Ir(ppy)₂acacmay have high quantum efficiency. Therefore, the fac body may not benecessarily preferred. In addition, when the complex is synthesized, itis difficult to synthesize one of constitutional isomers alternativelyand a mixture of both isomers may be used from the aspect of cost.

Specific examples of the organic metal complex of the present inventionare described below. However, the present invention is not limitedthereto.

Next, the organic light emitting device of the present invention isdescribed in detail.

The organic light emitting device of the present invention includes ananode, a cathode, and a layer formed of an organic compound, which issandwiched between the anode and the cathode.

Hereinafter, embodiments of the organic light emitting device of thepresent invention are described.

A first embodiment of an organic light emitting device according to thepresent invention includes the anode, the organic emission layer, andthe cathode, which are sequentially formed on a substrate. The firstembodiment is useful in a case where the emission layer is formed of anorganic compound which has all the properties including a holetransporting ability, an electron transporting ability, and lightemitting property. Further, in a case where the emission layer is formedof a mixture of compounds each having one of the hole transportingability, the electron transporting ability, and the light emittingproperty.

A second embodiment of the organic light emitting device according tothe present invention includes the anode, a hole transport layer, anelectron transport layer, and the cathode, which are sequentially formedon the substrate. The second embodiment is useful in a case where anorganic compound which is a light emitting substance having one of holetransporting property and electron transporting property and an organiccompound having electron transporting property alone or holetransporting property alone are used in combination. In addition, inthis second embodiment, the hole transport layer or the electrontransport layer serves as the emission layer.

A third embodiment of the organic light emitting device according to thepresent invention includes the anode, the hole transport layer, theemission layer, the electron transport layer, and the cathode, which aresequentially formed on the substrate. The third embodiment provides thelight emitting device, in which a carrier transporting function and alight emitting function are separated from each other. Thus, the devicecan be used appropriately in combination with organic compounds eachhaving one of the hole transporting property, electron transportingproperty, and light emitting property. Therefore, in the thirdembodiment, the degree of freedom in selection of a material extremelyincreases as well as various compounds different from each other inemission wavelength can be used. As a result, the range of luminescentcolors can be widened. Further, a light emitting efficiency of theorganic light emitting device can be improved by effectively trappingeach carrier or exciton in the central emission layer.

A fourth embodiment of the organic light emitting device according tothe present invention includes the anode, a hole injection layer, thehole transport layer, the emission layer, and the cathode, which aresequentially formed on the substrate. In the fourth embodiment, theprovision of the hole injection layer in between the anode and the holetransport layer imparts an improving effect on adhesiveness and the holeinjection property, and is effective for a reduction in voltage at whichthe device is driven.

A fifth embodiment of the organic light emitting device according to thepresent invention includes the anode, the hole transport layer, theemission layer, a hole/exciton blocking layer, the electron transportlayer, and the cathode, which are sequentially formed on substrate. Inthe fifth embodiment, a layer for inhibiting the escape of a hole orexciton toward the side of the cathode, which is the hole/excitonblocking layer, is provided between the emission layer and the electrontransport layer. The use of a composition material having an extremelyhigh ionization potential as a constituent material of the hole/excitonblocking layer is effective for improving the light emitting efficiency.

It should be noted that the device structures as described in the firstto fifth embodiments are each merely very basic device structure, andthe structure of the organic light emitting device of the presentinvention is not limited thereto. A variety of a layer structure may beprovided. For example: an insulating layer, an adhesive layer, or aninterference layer may be provided onto an interface between anelectrode and an organic compound, and a hole transport layer may beformed of two layers having different ionization potentials.

In the organic light emitting device of the present invention, theorganic metal complex of the present invention can be used in any one ofthe first to fifth embodiments. Here, the organic light emitting deviceof the present invention includes the organic metal complex of thepresent invention in a layer formed of an organic compound (organiccompound layer). Here, the term “organic compound layer” refers to, forexample, any one of the hole injection layer, the hole transport layer,the emission layer, the hole/exciton blocking layer, and the electrontransport layer indicated in the first to fifth embodiments. Preferredis the emission layer.

In the organic light emitting device of the present invention, theemission layer may be formed only of the organic metal complex of thepresent invention, but preferably formed of a host and a guest. Here,the term “guest” refers to a compound having mainly a function of lightemission. On the other hand, the term “host” refers to a compoundpresent as a matrix around the guest in the emission layer and mainlyhaving a function of transporting a carrier and a function of providingan exciton energy to the guest.

Here, in the case where the emission layer of the organic light emittingdevice is formed of a host having a carrier transporting property and aguest, a main process to the light emission includes the followingseveral processes. Energy transfer and light emission in respectiveprocesses are caused by competition with various deactivation processes.

(1) Transport of an electron and a hole inside the emission layer

(2) Exciton generation of the host, Exciton generation of the guest 1

(3) Exciton energy transmittance among host molecules

(4) Exciton energy transfer from the host to the guest, excitongeneration of the guest 2

(5) light emission from guest molecules

In general, in order to increase the light emitting efficiency of theorganic light emitting device, an emission central material itself isdesired to have large light emitting quantum efficiency.

Here, the organic metal complex of the present invention has highquantum efficiency of light emission in a dilute solution, whereby highlight emitting efficiency can be expected in the case of using theorganic metal complex of the present invention as a constituent materialfor the organic light emitting device.

In the organic light emitting device according to the present invention,in the case of using the organic metal complex of the present inventionas a guest (dopant), examples of the corresponding host include iridiumcompounds, compounds shown in Table 1, and derivatives thereof.

TABLE 4

In addition to the above compounds, there are given, but of course thehost is not limited to, a fused-ring compounds (such as fluorenederivatives, naphthalene derivatives, carbazole derivatives, quinoxalinederivatives, and quinoline derivatives), organic aluminum complexes suchas tris(8-quinolilato)aluminum, organic zinc complexes, triphenyl aminederivatives, polymer derivatives such as poly(fluorene) derivatives, andpoly(phenylene) derivatives.

In addition, in the case of the organic metal complex of the presentinvention as a guest (dopant), a concentration of the guest ispreferably 0.01 wt % to 20 wt %, and more preferably 0.5 wt % to 10 wt %with respect to the host. In addition, by controlling the concentrationof the guest, the emission wavelength of the device can be lengthened byabout 5 nm to 20 nm.

Here, a compound having a hole transporting property, and a compoundhaving a light emitting property, or a compound having an electrontransporting property, each of which is a conventionally-knownlow-molecular-weight-based or polymer compound-based, can be used, asrequired, together with the organic metal complex of the presentinvention.

Hereinafter, examples of those compounds are given.

As the material having a hole injecting property, a material having ahigh hole transfer degree is preferred to facilitate the injection of ahole from an anode and to transport the injected hole to the emissionlayer. Examples of the low-molecular-weight-based or polymer-basedmaterial each having a hole injecting property include, but are notlimited to, trialrylamine derivatives, phenylenediamine derivatives,stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives,poly(vinylcarbazole), poly(thiophene), and other conductive polymers.

As the material having a light emitting property, Ir(ppy)₃, Pt(OEP),Ir(piq)₃, Alq₃, rubrene, coumarine, and the like are exemplified inaddition to the organic metal complex of the present invention.

The electron injection transporting material may be arbitrarily selectedfrom compounds each of which facilitates the injection of an electronfrom a cathode and has a function of transporting the injected electronto the emission layer. In addition, the material is selected inconsideration of, for example, a balance with the hole mobility of thehole transporting material. The materials having electron injectiontransporting abilities include, but are of course not limited to, anoxadiazole derivative, an oxazole derivative, a pyrazine derivative, atriazole derivative, a triazine derivative, a quinoline derivative, aquinoxaline derivative, a phenanthroline derivative, and anorganoaluminum complex.

As a material for constituting an anode, a material having as large awork function as possible is preferred. Examples of available materialsinclude: metal elements such as gold, platinum, silver, copper, nickel,palladium, cobalt, selenium, vanadium, and tungsten, and alloys thereof;and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tinoxide (ITO), and indium zinc oxide. Further, conductive polymers such aspolyaniline, polypyrrole, and polythiophene may also be used. Each ofthose electrode substances may be used singly. Alternatively, two ormore of them may also be used in combination. Further, the anode mayadopt any one of a single layer construction and a multilayerconstruction.

On the other hand, as a material constituting a cathode, a materialhaving as small a work function as possible is preferred. Examples ofavailable materials include: alkali metals such as lithium, alkali earthmetals such as calcium, and metal elements such as aluminum, titanium,manganese, silver, lead, and chromium. Alternatively, alloys incombination of those metal elements may also be used. For example,magnesium-silver, aluminum-lithium, and aluminum-magnesium can be used.Further, metal oxides such as indium tin oxide (ITO) may also be used.Each of those electrode substances may be used singly or in combinationof two or more. Further, the cathode may adopt any one of a single layerconstruction and a multilayer construction.

Substrates which may be used in the organic light emitting device of thepresent invention include: opaque substrates such as metallic substratesand ceramics substrates; and transparent substrates such as glass,quartz, and plastic sheet substrates, but are not particularly limitedto these materials. In addition, a color filter film, a fluorescentcolor converting film, a dielectric reflection film, or the like may beused in the substrate to control emitted light.

It should be noted that, a protective layer or a sealing layer may beformed on the prepared device to prevent the device from contacting withoxygen, moisture, or the like. The protective layer may include adiamond thin film, a film made of an inorganic material such as metaloxide or metal nitride, a polymer film made of a fluorine resin,polyethylene, a silicone resin, a polystyrene resin, or the like, or mayinclude a photo-curing resin or the like. Further, the device itself canbe covered with glass, a gas-impermeable film, a metal, or the like andpackaged with an appropriate sealing resin.

Moreover, with respect to a direction of extracting light of the device,both a bottom emission structure (structure in which light is extractedfrom the substrate side) and a top emission structure (structure inwhich light is extracted from a side opposite to the substrate) can beacceptable.

In the organic light emitting device of the present invention, a layercontaining the organic metal complex of the present invention and alayer containing another organic compound are formed by a methoddescribed below. In general, such layers are produced using a vacuumdeposition method, ionization-assisted deposition method, a sputteringmethod, or a plasma method, or a thin film may be formed by dissolvingthe compound in a suitable solvent and subjecting the resultant to aknown coating method (e.g., a spin coating method, a dipping method, acasting method, an LB method, an ink jet method, etc.). Here, a layerformed by the vacuum deposition method, a solution coating method, orthe like is preferred because crystallization is less likely to occurand has excellent stability with time. In film formation by the coatingmethod, a film may be formed by using a compound in combination with anappropriate binder resin.

When the coating method is used, an oligomer or a polymer material maybe used as a host. In this time, the oligomer or the polymer materialcan be mixed with the organic metal complex of the present invention andthen coated, whereby a thin film having a good film-forming property canbe obtained.

The organic light emitting device is produced specifically in thefollowing processes.

(a) An ITO is patterned on a glass substrate to form an anode.

(b) PEDOT (for organic EL) manufactured by Bayer AG is dropped on theanode and spin-coated, followed by drying to form a hole transportlayer.

(c) A coating solution prepared from H-4 shown below, A21 (a weightmixing ratio: H-4/A21=10/1), and a solvent is dropped and spin-coated,followed by drying to form an emission layer.

(d) An electron transport layer such as Bphen is deposited under vacuum.

(e) KF is deposited under vacuum, whereby a first metal electrode isformed.

(f) A1 is deposited under vacuum, whereby a second metal electrode isformed.

Examples of the binder resin include, but of course are not limited to,a polyvinylcarbazole resin, a polycarbonate resin, a polyester resin, anABS resin, an acrylic resin, a polyimide resin, a phenol resin, an epoxyresin, a silicone resin, and a urea resin. In addition, these binderresins each may be formed of a homopolymer or a copolymer. In addition,one kind of the binder resin may be used alone or a mixture of two ormore kinds may be used. Further, a known additive such as plasticizer,an antioxidant, or a UV absorber, as required, may be used incombination.

By various known ideas, the organic light emitting device of the presentinvention can be improved in light-extraction efficiency, color purity,and the like. For example, by processing a shape of a substrate surface(for example, forming a fine concavo-convex pattern), controllingrefractive indices of the substrate, the ITO layer, or the organiclayer, controlling film thickness of the substrate, the ITO layer, orthe organic layer, and the like, the light-extraction efficiency and theexternal quantum efficiency can be improved. In addition, by methodsinvolving reducing extra wavelength component as a result of using amicrocavity structure (fine resonator structure) or obtaining a desiredcolor as a result of providing a color filter, the color purity can beimproved.

The organic light emitting device of the present invention may be aso-called top emission system in which a light emission is extractedfrom an anode side for the purpose of improving an aperture ratio or maybe a cavity structure in which the color purity is adjusted by a lightinterference.

The organic light emitting device of the present invention can beapplied to products which requires energy conservation and highluminance. The device may be applied to image display apparatuses, alight source of printers, lighting equipment, backlight of liquidcrystal displays, and the like.

As the image display apparatuses, an energy-conservation flat paneldisplay having high visibility and light-weight are exemplified.

In addition, as the light source of a printer, a laser light source partof a laser beam, which is widely used at present, can be substituted bythe organic light emitting device of the present invention. As themethod of substituting, a method involving arranging, on an array, anorganic light emitting device which can address independently isexemplified. Even if the laser light source part is substituted by theorganic light emitting device of the present invention, an image isformed by exposing to a photosensitive drum desirably as isconventionally done. Here, according to use of the organic lightemitting device of the present invention, a volume of the printer can belargely reduced.

An energy conservation effect can be expected in the lighting equipmentand the backlight by using the organic light emitting device of thepresent invention.

Next, the display apparatus using the organic light emitting device ofthe present invention is described. The display apparatus is providedwith the organic light emitting device of the present invention and aunit for supplying an electrical signal to the organic light emittingdevice of the present invention. Hereinafter, with reference to thefigures and taking an active matrix system as an example, the displayapparatus of the present invention is described in detail.

First, reference numerals in the figures are described. A displayapparatus 1 includes a pixel circuit 14, a scanning signal driver 11, aninformation signal driver 12, and a current supplying source 13. A pixelcircuit 2 includes a first thin film transistor (TFT) 21, a condenser 22(C_(add)), and a second thin film transistor (TFT) 23. A displayapparatus 3 includes a substrate 31, a moistureproof layer 32, a gateelectrode 33, a gate insulating layer 34, a semiconductor layer 35, adrain electrode 36, a source electrode 37, a TFT device 38, aninsulating layer 39, a contact hole 310 (through hole), an anode 311, anorganic layer 312, a cathode 313, a first protective layer 314, and asecond protective layer 315.

FIG. 1 illustrates an embodiment of a display apparatus. In addition,FIG. 1 illustrates schematically a structural example of the displayapparatus including the organic light emitting device of the presentinvention and a driving unit. In the display apparatus of FIG. 1, thescanning signal driver 11, the information signal driver 12, the currentsupplying source 13 are provided and the drivers and source areconnected to a gate selection line G, an information signal line I, anda current supplying line C, respectively. The pixel circuit 14 isprovided on an intersection point of the gate selection line G and theinformation signal line I. The scanning signal driver 11 selects gateselection lines from G1 to Gn subsequently, and then an image signal isapplied to the pixel circuit 14 through any one of information signallines I1 to In from the synchronized information signal driver 12.

Next, operation of the pixels is described. FIG. 2 is a circuit diagramillustrating a circuit which forms one pixel provided in the displayapparatus of FIG. 1. In the pixel circuit 2 of FIG. 2, when a selectionsignal is applied to a gate selection line Gi, the first thin filmtransistor (TFT1) 21 is switched to ON, and then an image signal Ii issupplied to the condenser (C_(add)) 22, whereby a gate voltage of thesecond thin film transistor (TFT2) 23 is determined. To the organiclight emitting device 24, a current is supplied from the currentsupplying line Ci according to the gate voltage of the second thin filmtransistor (TFT2) 23. Here, the gate voltage of the second thin filmtransistor (TFT2) 23 is retained by the condenser (C_(add)) 22 until thefirst thin film transistor (TFT1) 21 is next selected for scanning.Therefore, the current continues to be applied to the organic lightemitting device 24 until the next scanning is conducted. From theforegoing, the organic light emitting device 24 can emit lightconsistently during one frame.

FIG. 3 is a schematic drawing illustrating an example of a crosssectional structure of a TFT substrate used in the display apparatus ofFIG. 1. The structure is described in detail below by illustrating oneexample of a production process of the TFT substrate. When the displayapparatus 3 of FIG. 3 is produced, the moistureproof layer 32 is coatedon the substrate 31 such as a glass to protect a member (a TFT or anorganic layer) provided above the substrate. As a material forming themoistureproof layer 32, silicon oxide, a complex of silicon oxide andsilicon nitride, or the like is used. Next, a metal such as Cr is formedinto a film by sputtering, whereby the metal is patterned into apredetermined circuit shape to form the gate electrode 33. Subsequently,silicon oxide or the like is formed into a film by a plasma CVD method,a catalytic chemical vapor deposition method (cat-CVD method), or thelike, and the film is then patterned to form the gate insulating layer34. Next, by the plasma CVD method (in some cases, annealed at atemperature of 290° C. or higher), a silicon film is formed and patteredaccording to the circuit shape, whereby the semiconductor layer 35 isformed.

Further, the drain electrode 36 and the source electrode 37 are providedon the semiconductor layer 35, whereby the TFT device 38 is produced toform the circuit as shown in FIG. 2. Next, the insulating layer 39 isformed above the TFT device 38. Then, the contact hole (through hole)310 is formed so that the anode 311 for the organic light emittingdevice formed of a metal and the source electrode 37 are connected.

On the anode 311, the organic layer 312 formed of a single layer or amultilayer, and the cathode 313 are laminated subsequently, whereby thedisplay apparatus 3 can be obtained. At this time, in order to preventdegradation of the organic light emitting device, the first protectivelayer 314 or the second protective layer 315 may be provided. Accordingto driving of the display apparatus using the organic light emittingdevice of the present invention, display of favorable image quality fora long time can be obtained.

Note that the device is not limited to the switching device, and amonocrystalline silicon substrate, MIM device, a-Si type, or the likecan be easily applied to the above display apparatus.

Hereinafter, the present invention is described more specifically by wayof examples, but the present invention is not limited thereto.

<Example 1> (Synthesis of Exemplified Compound B-20)

(1) The following regents and solvent were loaded in a 500-ml reactor.

Compound F1: 25 g (113 mmol)N-bromosuccinyl imide: 24.1 g (135 mmol)Benzoyl peroxide: 2.74 gCarbon tetrachloride: 357 ml

Next, the inside of the reactor was made an argon atmosphere, and thereaction solution was then stirred for 2 hours while heated at 80° C.Next, after the reaction solution was cooled, a crystal was deposited byadding isopropyl ether to the solution. The precipitated crystal wasfiltered, and the resultant crystal was then washed with a little amountof isopropyl ether, and dried, whereby 26.3 g of Compound F2 as a browncrystal was obtained (yield 77%).

(2) The following regents and solvents were loaded in a 200-ml reactor.

Compound F2: 14 g (46.7 mmol)2-nitropropane: 4.37 g (49 mmol)

Ethanol: 80 ml

Next, the inside of the reactor was made an argon atmosphere, and 15.9 g(46.7 mmol) of 20% sodium ethoxide were added into the reactor. Afterthat, the reaction solution was stirred for 18 hours while heated at 40°C. The reaction solution was cooled, followed by vacuum concentration.Next, the obtained concentrate was subjected to a solvent extractiontwice with 100 ml of ethyl acetate, whereby an organic layer wascollected. Next, the organic layer was washed with water and a saturatedsalt solution sequentially, and then dried with magnesium sulfate. Next,the filtrate obtained by filtration of the organic layer wasconcentrated under vacuum, whereby a brownish-red solid was obtained.The solid was washed with a mixed solution containing isopropyl etherand hexane at 1:1, and then dried, whereby 8.07 g of Compound F3 as apale brown crystal were obtained (yield 73%).

(3) The following regents and solvent were loaded in a 50-ml reactor.

Compound F3: 8 g (34.0 mmol)

Tetrahydrofuran: 10 ml

tert-butyl amine: 7.47 g

Next, 3 ml of distilled water were added to the reaction solution,followed by stirring at room temperature for 24 hours. After thecompletion of the reaction, the reaction solution was concentrated undervacuum. Next, after 20 ml of water were added to the solution, theobtained solution was subjected to a solvent extraction twice with 50 mlof diethyl ether, whereby an organic layer was collected. Next, thecollected organic layer was washed with water once, then washed with asaturated salt solution once, and dried with magnesium sulfate. Next,the obtained filtrate by filtration of the organic layer wasconcentrated under vacuum, whereby 9.68 g of Compound F4 as a brownsolid were obtained (yield 99%).

(4) The following regents and solvent were loaded in a 300-ml reactor.

Bis(1,5-cyclooctadiene)nickel: 0.36 mg (1.31 mmol)Tris(o-tolyl)phosphine: 0.796 g (2.62 mmol)Sodium carbonate: 2.77 g (26.2 mmol)Degassed dimethylformamide: 80 ml

Next, the inside of the reactor was made an argon atmosphere, and thereaction solution was then stirred for 30 minutes. After that, thefollowing reagents were further added.

Compound F4: 7.59 g (26.2 mmol)Phenyl acetylene (Compound F5): 5.34 g (52.3 mmol)

Next, the reaction solution was stirred for 3 hours while heated at 100°C. Next, the reaction solution was cooled and water was added thereto,and then the solution was concentrated under vacuum. Next, the solutionwas subjected to a solvent extraction three times with 100 ml of amixture solvent containing isopropyl ether and ethyl acetate at 1:1,whereby an organic layer was collected. The organic layer was washedwith water and a saturated salt water sequentially, and then dried withmagnesium sulfate. Next, the filtrate obtained by filtration of theorganic layer was concentrated under vacuum, whereby a black liquidhaving viscosity was obtained. The liquid was subjected to columnchromatography (developing solvent: chloroform/ethyl acetate=20/1), andthen further subjected to column chromatography (developing solvent:hexane/ethyl acetate=5/1) for purifying, whereby a brown solid wasobtained. Next, the brown solid was dissolved in a little amount ofethyl acetate, and recrystallized by adding a solution containingisopropyl ether and hexane at 1:1. Next, the crystal obtained byrecrystallization was dried, whereby 4.2 g of Compound F6 as a palebrown crystal were obtained (yield 62%).

(5) The following regents and solvent were loaded in a 100-mlthree-necked flask.

Iridium (III) trihydrate: 0.658 g (3.74 mmol)Compound F6: 2.00 g (16 mmol)

Ethoxyethanol: 20 ml Water: 6 ml

Next, the reaction solution was stirred for 30 minutes at roomtemperature in a stream of nitrogen. Next, the reaction solution wasstirred for 10 hours while heated at 80° C. Next, the reaction solutionwas cooled to room temperature, and the deposited precipitate wasfiltered and washed with water, followed by washing with ethanol. Afterthe washing, the precipitate was dried under reduced pressure at roomtemperature, whereby 2.2 g of Compound F7 as a yellowish brown powderwere obtained (yield 80%).

(6) The following regents and solvents were loaded in a 100-mlthree-necked flask.

Ethoxyethanol: 45 ml

Compound F7: 2.2 g (1.48 mmol)Acetylacetone: 0.89 g (8.9 mmol)Sodium carbonate: 0.792 g (7.48 mmol)

Next, the reaction solution was stirred for 1 hour at room temperaturein a stream of nitrogen, and then stirred for 8 hours while heated at120° C. Next, a precipitate was deposited by cooling the reactionsolution with ice, and the deposited precipitate was filtered, followedby washing with water. Next, the precipitate was washed with ethanol,dissolved in chloroform, and an insoluble matter was filtered. Next, theobtained filtrate was concentrated, and recrystallized with achloroform-methanol mixture solvent, whereby 0.42 g of ExemplifiedCompound B20 as a yellowish brown powder was obtained (yield 35%).

In addition, the structure of the compound was confirmed with an NMRmeasurement.

¹H-NMR (CDCl₃, 400 MHz) σ (ppm): 9.22 (s, 2H), 8.99 (s, 2H), 8.85 (d,2H, J=7.6 Hz), 7.97 (d, 2H, J=8.0 Hz), 7.86 (m, 10H, J=8.8 Hz), 6.88 (t,2H, J=6.8 Hz), 6.65 (t, 2H, J=6.4 Hz), 6.26 (d, 3H, J=7.6 Hz), 5.27 (s,1H), 1.84 (s, 6H).

Further, an emission spectrum (PL spectrum) of Exemplified Compound B20in a 1×10⁻⁵ mol/l toluene solution was measured using F-4500manufactured by Hitachi, Ltd. Specifically, photoluminescence (PL) at anexcitation wavelength of 450 nm was measured. As a result, a PL spectrumhaving a maximum peak intensity at 538 nm as illustrated in FIG. 4 wasobtained.

On the other hand, a quantum efficiency of Exemplified Compound B20 wascalculated from an absorbance and a light emission area of the compounditself. The result is shown in Table 5. Note that the absorbance wasevaluated from an absorbent spectrum in a 1×10⁻⁵ mol/l toluene solutionwhich was measured by using a ultraviolet and visible spectrophotometerV-560 manufactured by JASCO Corporation.

<Example 2> (Synthesis of Exemplified Compound B1)

The following regents and solvent were loaded in a 50-ml three-neckedflask.

Glycerol: 10 ml

Exemplified Compound B20: 0.5 g (0.625 mmol)Compound E06: 0.319 g (1.25 mmol)

Next, the reaction solution was stirred for 8 hours in a stream ofnitrogen while heated at 200° C. Next, 20 ml of water were added to thereaction solution, followed by further stirring. Then, the depositedprecipitate was filtered, and washed with ethanol. The precipitate wasfiltered with dimethyl formamide upon heating, and thereafter,recrystallized by cooling, whereby 0.301 g of Exemplified Compound B1 asa yellowish brown powder was obtained (yield 50%).

In addition, the structure of the compound was confirmed by an NMRmeasurement.

¹H-NMR (CDCl₃, 400 MHz) σ (ppm): 9.08 (s, 3H), 8.81 (d, 3H, J=8.4 Hz),8.23 (s, 3H), 8.98 (d, 3H, J=7.2 Hz), 7.85 (d, 3H, J=6.4 Hz), 7.73 (m,9H, J=6.8 Hz), 7.57 (d, 3H, J=8.4 Hz), 7.28 (m, 3H, J=8.4 Hz), 6.99 (t,3H, J=7.2 Hz), 6.88 (d, 3H, J=7.2 Hz).

Further, a PL spectrum of Exemplified Compound B1 was measured in a1×10⁻⁵ mol/l toluene solution in the same manner as in Example 1(excitation wavelength: 450 nm). As a result, the PL spectrum having amaximum peak wavelength at 536 nm as illustrated in FIG. 5 was obtained.On the other hand, the quantum efficiency of Exemplified Compound B1 wascalculated in the same manner as in Example 1. Results are shown inTable 5.

Comparative Example 1

Organic Metal Complex K1 shown below was synthesized and the PL spectrumwas measured in the same manner as in Example 1. In addition, thequantum efficiency was calculated in the same manner as in Example 1.Results were shown in Table 5.

TABLE 5 Maximum peak wavelength Quantum (mm) efficiency Example 1Exemplified 538 1.3^((Remark)) Compound B20 Example 2 Exemplified 5361.3^((Remark)) Compound B1 Comparative K1 514 1.0^((Remark)) Example 1^((Remark))the quantum efficiency is a relative quantum efficiency whenthe quantum efficiency of K1 is defined as 1.0.

From Table 5, when the PL spectra of the organic metal complexes inExamples 1 and 2 and Organic Metal Complex K1 were compared, the organicmetal complexes in Examples 1 and 2 each had a maximum peak wavelengthat a longer wavelength side than that of Organic Metal Complex K1, anddifference of the maximum peak wavelength between the complexes inExamples 1 and 2 and Organic Metal Complex K1 was small. This is becausean aromatic ring was fused non-linearly with respect to a basic skeletoncontaining nitrogen which forms a coordinate bond with an iridium atomand lengthening of the emission wavelength could be prevented. Inaddition, from FIG. 5, it was indicated that the quantum efficiency ofthe organic metal complexes of Examples 1 and 2 was higher than that ofOrganic Metal Complex K1. The reason may be as follows. The aromaticring was fused to the basic skeleton containing nitrogen which forms acoordinate bond with an iridium atom in a direction away from theiridium atom, whereby the oscillator strength of molecules themselveswas improved. As a result, the quantum efficiency was improved.

<Example 3> (Synthesis of Exemplified Compound A30)

1.5 g (2 mmol) of Exemplified Compound A30 were obtained by a reactionaccording to the method in Example 1 except that Compound F6 was changedto Compound F8 (3 g, 0.012 mol) in the section (5) of Example 1.

In addition, the structure of Compound A30 was confirmed by an NMRmeasurement.

¹H-NMR (CDCl₃, 400 MHz) σ (ppm): 8.86 (d, 2H, J=9.2 Hz), 8.72 (m, 4H,J=6.8 Hz), 8.30 (d, 2H, J=6.4 Hz), 8.18 (d, 2H, J=8.0 Hz), 7.98 (m, 4H,J=9.6 Hz), 7.76 (m, 4H, J=4.0 Hz), 6.91 (t, 2H, J=7.2 Hz), 6.66 (t, 2H,J=7.6 Hz), 6.13 (d, 2H, J=6.4 Hz), 5.23 (s, 1H), 1.78 (s, 6H).

Further, a PL spectrum of Exemplified Compound A30 was measured in a1×10⁻⁵ mol/l toluene solution in the same manner as in Example 1(excitation wavelength: 510 nm). As a result, the PL spectrum having amaximum peak wavelength at 601 nm as illustrated in FIG. 6 was obtained.On the other hand, the quantum efficiency of Exemplified Compound A30was calculated in the same manner as in Example 1. Results are shown inTable 6.

<Example 4> (Synthesis of Exemplified Compound A1)

0.2 g (0.2 mol) of Exemplified Compound A1 was obtained by a reactionaccording to the method in Example 2 except that Exemplified CompoundA30 (0.8 g, 1 mmol) instead of Exemplified Compound B20 and Compound F8(0.63 g, 2.5 mol) instead of Compound F6 were used.

In addition, the structure of Compound A1 was confirmed by an NMRmeasurement.

¹H-NMR (CDCl₃, 400 MHz) σ (ppm): 8.85 (d, 3H, J=8.0 Hz), 8.48 (d, 3H,J=8.0 Hz), 8.18 (d, 3H, J=7.6 Hz), 7.92 (m, 9H, J=6.4 Hz), 7.68 (m, 6H,J=6.8 Hz), 7.53 (d, 3H, J=6.4 Hz), 7.07 (d, 3H, J=7.2 Hz), 7.01 (t, 3H,J=7.2 Hz), 6.91 (t, 3H, J=7.2 Hz).

Further, a PL spectrum of Exemplified Compound B1 was measured in a1×10⁻⁵ mol/l toluene solution in the same manner as in Example 1(excitation wavelength: 510 nm). As a result, the PL spectrum having amaximum peak wavelength at 592 nm as illustrated in FIG. 7 was obtained.On the other hand, the quantum efficiency of Exemplified Compound A1 wascalculated in the same manner as in Example 3. Results are shown inTable 6.

Comparative Example 2

Organic Metal Complex K2 shown below was synthesized, whereby a PLspectrum was measured in the same manner as in Example 1. In addition, aquantum efficiency was calculated in the same manner as in Example 3.Results were shown in Table 6.

TABLE 6 Maximum peak wavelength Quantum (mm) efficiency Example 3Exemplified 601 1.6^((Remark)) Compound A30 Example 4 Exemplified 5921.6^((Remark)) Compound A1 Comparative K2 619 1.0^((Remark)) Example 1^((Remark))the quantum efficiency is a relative quantum efficiency whenthe quantum efficiency of K2 is defined as 1.0.

From Table 6, when the PL spectra of the organic metal complexes inExamples 3 and 4 and Organic Metal Complex K2 were compared, the organicmetal complexes in Examples 3 and 4 each had a maximum peak wavelengthat a shorter wavelength side than that of Organic Metal Complex K2. Thisis because an aromatic ring was fused non-linearly with respect to abasic skeleton containing nitrogen which forms a coordinate bond with aniridium atom and lengthening of the emitting light wavelength could beprevented. In addition, from Table 6, it was indicated that the quantumefficiency of the organic metal complexes of Examples 3 and 4 was higherthan that of Organic Metal Complex K2. The reason may be as follows. Thearomatic ring was fused to a basic skeleton containing nitrogen whichforms a coordinate bond with an iridium atom in a direction away fromthe iridium atom, whereby the oscillator strength of moleculesthemselves was improved. As a result, the quantum efficiency wasimproved.

Example 5

An organic light emitting device in which an anode, a hole transportlayer, an emission layer, an electron transport layer, and a cathodewere provided on a substrate sequentially was produced.

First, an ITO was patterned on a glass substrate to form an anode. Atthis time, a film thickness of the anode was set to 100 nm, and anelectrode area was set to 3 mm².

Next, in a vacuum chamber at 10⁻⁵ Pa, the following organic compoundlayer and electrode layer were continuously formed into a film on theanode by vacuum deposition with resistance heating. Specifically, H-1shown below was deposited to form a hole transport layer. At this time,a film thickness of the hole transport layer was set to 20 nm. Next, H-2shown below as a host and Exemplified Compound A1 as a guest wereco-deposited so that an amount of the guest became 5 wt % with respectto the host, whereby an emission layer was formed. In this time, a filmthickness of the emission layer was set to 30 nm. Then, H-3 below wasdeposited to form an electron transport layer. In this time, a filmthickness of the electron transport layer was set to 30 nm. Next, KF wasdeposited to form a first metal electrode layer. In this time, a filmthickness of the first metal electrode layer was set to 1 nm. Next, A1was deposited, whereby a second metal electrode was formed. In thistime, a film thickness of the second metal electrode layer was set to100 nm. Note that the first metal electrode layer and the second metalelectrode layer each function as a cathode. As described above, theorganic light emitting device was obtained.

A current-voltage characteristic of the obtained device was measuredusing a minute current ammeter 4140B manufactured by Hewlett-PackardDevelopment Company, L.P. In addition, emission characteristics of theobtained device were measured with BM7 manufactured by TOPCONCORPORATION. Note that when respective characteristics were measured, anemission luminance was set to 1,000 cd/m². Measured results are shown inTable 7.

Example 6

An organic light emitting device was formed in the same manner as inExample 5 except that an emission layer was formed by co-deposition sothat an amount of a guest was 15 wt % with respect to a host. Inaddition, emission characteristics of the obtained device were measuredin the same manner as in Example 5. Results are shown in Table 7.

Example 7

An organic light emitting device was formed in the same manner as inExample 5 except that Exemplified Compound A1 as a guest was changed toExemplified Compound B1. In addition, emission characteristics of theobtained device were measured in the same manner as in Example 5.Results are shown in Table 7.

TABLE 7 Emission Light emitting wavelength efficiency Voltage (nm)(cd/A) (V) Example 5 595 25 3.5 Example 6 610 17 3.4 Example 7 535 504.0

This application claims the benefit of Japanese Patent application No.2007-290548, filed Nov. 8, 2007, which is hereby incorporated byreference herein in its entirety.

1.-5. (canceled)
 6. A method of manufacturing a device, the methodcomprising: preparing a substrate provided with one of an anode or acathode; forming an organic compound layer; forming the other of theanode or the cathode; wherein the organic compound layer comprising ametal complex having a structure represented by the following generalformula (1):ML_(m)L′_(n)  (1) wherein L and L′, which are different from each other,each represent a bidentate ligand; wherein m represents an integer of 1to 3 and n represents an integer of 0 to 2, provided that m+n is 3;wherein M represents Ir; wherein the partial structure ML_(m) has astructure represented by the following general formula (8):

wherein the benzene ring with R₄₁-R₄₄ attached thereto in the formula(8) is further represented by any one of the following formulae:

wherein *1 shows the connection to the Ir; wherein *2 shows theconnection to the benzo[f]isoquinoline ring represented in the formula(8); wherein R₈₈ to R₁₀₂, which may be identical to or different fromeach other, each represent a hydrogen atom, a halogen atom, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted aralkyl group, an amino group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group; wherein the partial structure ML′_(n)has a structure represented by any one of the following general formulae(10) to (12):

wherein R₄₅ to R₅₂, which may be identical to or different from eachother, each represent a hydrogen atom, a halogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkoxy group,a substituted or unsubstituted aryloxy group, a substituted orunsubstituted aralkyl group, an amino group, a substituted orunsubstituted aryl group, or a substituted or unsubstituted heterocyclicgroup, and R₄₇ and R₄₈ may be bonded to form a benzene ring that isfused with the benzo[f]isoquinoline ring represented in the formula (8);and wherein R₆₅ to R₇₉, which may be identical to or different from eachother, each represent a hydrogen atom, a halogen atom, a substituted orunsubstituted alkyl group, an alkoxy group, an aralkyl group, asubstituted amino group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heterocyclic group, and adjacentsubstituents among R65 to R68 may be bonded to form a ring that is fusedwith the benzene ring represented in the formula (10), and adjacentsubstituents among R77 to R79 may be bonded to form a ring that is fusedwith the backbone represented in the formula (12).
 7. The methodaccording to claim 6, wherein the organic compound layer is formed by avacuum deposition method, ionization-assisted deposition method, asputtering method, a plasma method, or a coating method.
 8. The methodaccording to claim 7, wherein the coating method is an ink-jet method.9. The method according to claim 7, wherein the coating method isperformed with binder resin.
 10. The method according to claim 6,further comprising forming a transistor connected to the anode or thecathode.
 11. The method according to claim 10, the formation of theanode includes a patterning process.
 12. The method according to claim11, further comprising forming a protective layer disposed over thedevice.
 13. The method according to claim 12, further comprising forminga color filter disposed over the device.
 14. The method according toclaim 6, further comprising preparing a substrate; and forming amoistureproof layer over the substrate.
 15. A method of manufacturing adisplay apparatus, the method comprising: forming a plurality ofdevices; at least one of the devices is formed by the method accordingto claim
 6. 16. A method of a lighting apparatus, the method comprising:the method according to claim 6 and forming a transistor connected theanode or the cathode.